Characterization of the reaction products of epoxidised Adenopus breviflorus Benth. seed oil with sodium azide and trimethylsilyl azide

Epoxidised oil was prepared classically from Adenopus breviflorus Benth. seeds oil (ADBO) using formic acid/hydrogen peroxide. The epoxidised oil (EADBO) had hydroxyl value of 0, oxirane value of 5.2 and iodine value of 1.2 g I-2/100 g. Cleavage trials of the oxirane group of the epoxidised oil with different reactants were undertaken in order to produce new derivatives which were then characterized. Reaction of the EADBO with sodium azide/ammonium chloride mixture for 48 h led to complete opening of all epoxy groups and production of different azidohydrin compounds. The product had oxirane value of 0 and hydroxyl value of 220 mg KOH/g. Reaction of EADBO with trimethylsilyl azide in the presence of borontrifluoride etherate as acid catalyst only led to the acidolysis of triglyceride bond and the production of an acylazido compound and a silylated diepoxy diglyceride compound which would be very versatile for preparation of new lipid derivatives. These products were characterized by spectroscopic methods and discussed. (C) 2006 Elsevier B.V. All rights reserved.